Water → HCID 68688416、化合物

HRID 1175211ノート

反応式

HRID 1175211 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].CC1(C)C(C)(C)OB([C:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH2:27])O1.C([O-])([O-])=O.[K+].[K+].O>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:28]1([C:26]([C:2]2[CH:3]=[C:4]([CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)[CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])=[CH2:27])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

参加物

7

反応物 4

HCID 962Water2 回HCID 11430Potassium CarbonateHCID 110316711-Phenylvinylboronic acid, pinacol esterHCID 68689230HCID 68689230、化合物

生成物 1

HCID 68688416HCID 68688416、化合物

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

Methyl 3-bromo-5-(pyridin-2-yl)benzoate (137 mg, 0.47 mmol), 4,4,5,5-tetramethyl-2-(1-phenylvinyl)-1,3,2-dioxaborolane (162 mg, 0.70 mmol), Pd(PPh3)4 (19 mg, 0.023 mmol) and K2CO3 (195 mg, 1.41 mmol) were taken up in DME (5 mL) and water (1 mL) and heated to about 80° C. overnight. The reaction mixture was combined with water and the product was extracted into EtOAc (3×10 mL). The combined organic extracts were washed with water (1×10 mL), brine (1×10 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified via automated flash chromatography (silica gel; 0 to 25% EtOAc in hexanes) to afford methyl 3-(1-phenylvinyl)-5-(pyridin-2-yl)benzoate. MS m/z=316 [M+1]+. Calc'd for C21H17NO2: 315.

後処理

  1. extractionthe product was extracted into EtOAc (3×10 mL)
  2. washThe combined organic extracts were washed with water (1×10 mL), brine (1×10 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified

出典と根拠

ORDレコード
ord-7c44ea52a1824e0396215958e36c3e41
出典データセット
uspto-grants-2010_11
特許番号
US07838676B2

反応ノート

読み込み中…